FI60020C - SOM HERBICID ANVAENDBART 2-CARBOXYTHYL-N-PHOSPHONOMETHYLGLYCINATE OCH DESS SALTER - Google Patents

Description

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Patent and Registration Releases Anaekan utkgd och utUkrifMn published 31.07.8l (32) (33) (31) Pyr1 · »/ atuoikaui — Bagird prtoritct 21.11.73 USA (US) U17858 (71) Monsanto Company, 800 North Lindbergh Boulevard, St. Louis, Missouri 63166, USA (72) John Edvard Franz, Crestvood, Missouri, Hans Leopold Nufer, Creve Coeur, Missouri, USA (US) (7M Oy Kolster Ab (5t) 2-Carboxyethyl N-phosphonomethylglycinate for use as a herbicide This invention relates to a novel 2-carboxyethyl N-phosphonomethylglycinate and its salts which can be used as herbicides and to a process for their preparation.

The novel compounds of this invention, 2-carboxyethyl N-phosphonomethyl glycinate and its salts, have the formula ΜΌ "denotes sodium or isopropylammonium, and the others denote hydrogen.

The novel 2-carboxyethyl N-phosphonomethylglycinate of this invention is prepared by reacting an aqueous solution of N-phosphonomethylglycine with a lactone, such as propiolactone, in the presence of a base and then neutralizing the base with hydrochloric acid. The various salts are prepared by treating the free acid with a suitable base.

The reaction temperature is normally maintained at about 20 ° C, although higher or lower temperatures are possible.

The order of addition of the reactants is critical. It is important to add my illicit N-phosphonomethylglycine to the basic aqueous solution. For convenience and ease of isolation of N-phosphonomethylglycinate, equimolar amounts of lactone and N-phosphonomethylglycine are preferably used.

The reaction is normally carried out at a pressure of one atmosphere, although overpressures and underpressures may be used.

FI patent application 3000/71 (corresponding to U.S. Pat. No. 3,799,758) discloses herbicidally active alkyl and alkoxyalkyl esters of N-phosphonomethylglycine.

Herbicidal Experiments Experiment 1 The subsequent herbicidal activity of the compounds of this invention is shown as follows. The active ingredients are placed in spray form in IU or 21-day-old samples of different plant species. A spray, an aqueous solution containing the active ingredient and a surfactant (35 parts of dodecylbenzenesulfonic acid butylamine salt and 65 parts of tall oil condensed with ethylene oxide in a ratio of 11 moles of ethylene oxide per mole of tall oil per kg of ha). The treated plants are placed in a greenhouse and the effects are monitored and recorded after about 2 or U weeks as shown in Table I.

The herbicidal index used in Table I is as follows:

Plant reaction Index no damage 0 weak damage 1 average. damage 2 serious damage 3

dead U

3 60020

Table I

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1,1 212221001122 21222201113! i *, '^ 1+ 60020

Test 2

The herbicidal activity of the compounds according to the invention was compared with the herbicidal activity of the compounds according to FI patent application 3000/71 (corresponding to DE application publication 2 152 826). The compounds of the invention are the compounds (II and III) prepared in Examples 2 and 3, and the reference compounds are Compound III, which is disodium N-phosphonomethylglycinate, and Compound IV, which is the monoammonium salt of N-phosphonomethylglycine.

The test method is described above in Experiment 1. The herbic indices used in Table II are the same as in Table I.

The following plant species were used in Experiment 2:

Plant species A - soybean B - sugar beet C - Wheat D - rice E - sorghum F - bile grass G - wild buckwheat H - my day I - Sesbania Exaltata J - flour whey K - bitter buckwheat L - velvet leaf M - roofing buckwheat N - millet 0 - chicken millet - blood millet

Table II

Compound Observation time kg / ha Plant species

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II 1+ U 0100-10102-11223 III k U 1111-21102211223

Comparison of compound III 2 1 3 H li li 11 2 3 U 3 3 U l (VI 2 1 2m3m32hk-3hkkh

Marking - means that the plant in question was not available. - V * 5 60020

From the results (Table II), it can be seen that the reference compounds have a general herbicidal action and destroy not only weeds but also useful plants. On the other hand, the compounds according to the invention have a clear selective effect, so that, even in higher application rates, they do little to damage crops such as soybeans, sugar beet and rice. The weeds used in the experiments are those which occur especially in these cultures, so that the use of the compounds according to the invention as herbicides is very particularly advantageous.

For brevity and simplicity, the term "active ingredient" is hereinafter used to denote the compounds of this invention described so far.

In herbicidal compositions, the active ingredient may be mixed with one or more media, which may be solid or liquid excipients, diluents, diluents or the like. Herbicidal preparations include moisturizing powders, aqueous suspensions, dust preparations, emulsifiable oils and solutions in solvents. In general, these preparations may all contain one or more surfactants.

Surfactants that can be used in herbicidal formulations are well known to those skilled in the art and are well documented in U.S. patents, official publications, and textbooks. The preparation, formulations, and particle size of wetting powders, aqueous suspensions, dusts, emulsifiable oils and solutions are also well known to those skilled in the art and well documented. The active ingredient in herbicidal compositions is usually present in an amount of 0.5 to 95 parts by weight per 100 parts by weight of the wetting powder or dust preparations per 100 parts by weight of the emulsifiable oil preparations. Formulations containing amounts of the active ingredient other than those described above can be readily prepared by those skilled in the art.

The application of the herbicidal compositions of this invention to a plant is well known to those skilled in the art.

The application of liquid and in particular solid herbicidal preparations to the above-ground parts of the plants can be carried out by conventional methods, e.g. by spraying or spraying. The active ingredient may be mixed with one or more excipients, which may be solid or liquid diluents or carriers, or the like, to form herbicidal compositions. Herbicidal preparations, including moisturizing powders, aqueous suspensions, dust preparations, emulsifiable oils and solutions in solvents, contain the active ingredients of this invention.

In general, these preparations may all contain one or more surfactants. Herbicidal mixtures are used to produce a general herbicidal effect so that the active ingredient becomes 1.1, 50 <kg / ha.

60020 6

The following examples further illustrate the invention. In the examples, all parts and percentages are by weight unless otherwise indicated.

Example 1 A 500 ml round bottom flask was charged with N-phosphonomethylglycine (17 g), water (200 ml) and sodium hydroxide (12 g) and the mixture was stirred until a clear solution was obtained. The solution was cooled to 20 ° C and propiolactone (8 g) was added over 15 min. during stirring. Stirring was continued for 1 hour at room temperature. The reaction mixture was acidified with hydrochloric acid to give a solid which clouded the solution. The solid was removed by filtration and dried. The solid was identified as 2-carboxyethyl N-phosphonomethyl liglycinate (Compound 1), (m.p. 211 ° C, dec.), And gave the following elemental analysis:

Calculated Obtained C 29.79% 29.78% H 5.33% 5.08% N 5.79% 5.71% P 12.80% 12.63%

Example 2 An aqueous solution of the bis (isopropylamine) salt of 2-carboxyethyl N-phosphonomethylglycinate was prepared as follows: 2-Carboxyethyl N-phosphonomethylglycinate (kt0k g) was dissolved in water (5.0 g). Isopropylamine (1.92 g) was added to the mixture under cooling to give an aqueous solution containing the bis (isopropylamine) salt of 2-carboxyethyl N-phosphonomethylglycinate (Compound II). White, amorphous substance, softening point 82-5 ° C.

Example 3 2-Carboxyethyl N-phosphonomethylglycinate (* 4.0 g) was dissolved in water (5.28 g). Sodium hydroxide (1.36 g) was added to the mixture under cooling to give an aqueous solution containing disodium (2-carboxyethyl) -N- (phosphonomethyl) glycinate (Compound III). White, amorphous substance, softens at 75 ~ 85 ° C.

Analysis showed it to be a dihydrate.

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Claims (2)

7 60020 2. 2-Carboxyethyl N-phosphonomethylglycinate and its salts for use as a herbicide, having the formula: / v 0 H 0 0 'P-CHg -NC Hg -C-O- (Cl up to two of M ', M' and M represent sodium or isopropyl ammonium, and the others represent hydrogen. 2. A process for the preparation of 2-carboxyethyl N-phosphonomethylglycinate and its salts for use as a herbicide, having the formula: ΜΌ v 0 H 0 0 'P-CH2-N-CH2-C-O- (CHgJgC -OM wherein not more than two of the groups M *, M "and M denote sodium or isopropylammonium, and the others denote hydrogen, characterized in that a mixture of N-phosphonomethylglycine, water and base is treated with propiolactone, the base is neutralized and, if desired, the compound obtained is converted into a salt with a suitable base.